Isolation of Mangiferin from Bombax malabaricum and Structure Revision of Shamimin

Abstract

Repeated column chromatography of the n-BuOH fraction of the 70 % EtOH of the dried leaves of Bombax malabaricum led to the isolation of mangiferin, a xanthone. Mangiferin was identified by UV, ¹H- and ¹³C-NMR spectroscopy and electrospray mass spectrometry. It was found to be identical to shamimin, a compound for which originally a flavonol structure was proposed, and the structure of which has to be revised.

References

• 1 Chanda Y R. The Wealth of India, Raw Material. Vol. IX New Delhi; CSIR Hillside Rood 1962: pp. 175-83
• 2 Bircher W H. Gardens of Hesperides. Cairo; The Anglo-Egyptian Book Shop 1960
• 3 Nadkarni K M. The Indian Materia Medica. Bombay; Popular Parkashan 1976: pp. 207-9
• 4 MacDonald Hocking G. A Dictionary of Natural Products. Medford; Plexus Publishing, Inc 1997: p. 119
• 5 Saleem R, Ahmad M, Hussain S, Qazi A M, Ahmad S I, Qazi M H, Ali M, Faizi S, Akhtar S, Hussain S N. Hypotensive, hypoglycaemic and toxicological studies on the flavonol C-glycoside shamimin from Bombax ceiba .  Planta Med. 1999;  65 331-4
• 6 Faizi S, Ali M. Shamimin: A new flavonol C-glycoside from leaves of Bombax ceiba .  Planta Med. 1999;  65 383-5
• 7 Hano Y, Matsumoto Y, Shinohara K, Sun J -Y, Nomura T. Structures of four new isoprenylated xanthones, cudraxanthones L, M, N, and O from Cudrania tricuspidata .  Planta Med. 1991;  57 172-5
• 8 Wada H, Shimizu Y, Tanaka N, Cambie R C, Braggins J E. Chemical and chemotaxonomical studies of ferns. LXXXVII. Constituents of Trichomanes reniforme .  Chem Pharm Bull. 1995;  43 461-5
• 9 Aritomi M, Komori T, Kawasai T. Massenspektren von Isomangiferin und Mangiferin sowie verwandter peracetylierter C-Glucoside.  Liebigs Ann Chem. 1970;  734 91-101
• 10 Faizi S, Muhammad  A. ¹H and ¹³C NMR of acetyl derivatives of shamimin, a flavonol C-glycoside.  Magn Reson Chem. 2000;  38 701-3
• 11 Hostettmann K, Hostettmann M. Xanthones. In: Dey PM, Harborne JB, editors Methods in Plant Biochemistry Vol. 1 Plant Phenolics. London; Academic Press 1989: pp. 493-508
• 12 Markham K R. Techniques of Flavonoid Identification. London; Academic Press 1982: pp. 36-51